diff --git a/native/libwinbridge/bridge.cpp b/native/libwinbridge/bridge.cpp
index 309395c..f83e26b 100644
--- a/native/libwinbridge/bridge.cpp
+++ b/native/libwinbridge/bridge.cpp
@@ -31,6 +31,9 @@
 #include <strsafe.h>
 #include <shellapi.h>
 
+#pragma comment( lib, "gdiplus.lib" )
+#include <gdiplus.h>
+
 // How many milliseconds must pass between keystrokes to refresh the keyboard layout
 const long refreshKeyboardLayoutInterval = 2000;
 
@@ -656,3 +659,43 @@ int32_t get_clipboard(wchar_t *buffer, int32_t size) {
 
     CloseClipboard();
 }
+
+int32_t set_clipboard_image(wchar_t *path) {
+    bool result = false;
+
+    Gdiplus::GdiplusStartupInput gdiplusStartupInput;
+    ULONG_PTR gdiplusToken;
+    Gdiplus::GdiplusStartup(&gdiplusToken, &gdiplusStartupInput, NULL);
+
+    Gdiplus::Bitmap *gdibmp = Gdiplus::Bitmap::FromFile(path);
+    if (gdibmp)
+    {
+        HBITMAP hbitmap;
+        gdibmp->GetHBITMAP(0, &hbitmap);
+        if (OpenClipboard(NULL))
+        {
+            EmptyClipboard();
+            DIBSECTION ds;
+            if (GetObject(hbitmap, sizeof(DIBSECTION), &ds))
+            {
+                HDC hdc = GetDC(HWND_DESKTOP);
+                //create compatible bitmap (get DDB from DIB)
+                HBITMAP hbitmap_ddb = CreateDIBitmap(hdc, &ds.dsBmih, CBM_INIT,
+                                                     ds.dsBm.bmBits, (BITMAPINFO*)&ds.dsBmih, DIB_RGB_COLORS);
+                ReleaseDC(HWND_DESKTOP, hdc);
+                SetClipboardData(CF_BITMAP, hbitmap_ddb);
+                DeleteObject(hbitmap_ddb);
+                result = true;
+            }
+            CloseClipboard();
+        }
+
+        //cleanup:
+        DeleteObject(hbitmap);
+        delete gdibmp;
+    }
+
+    Gdiplus::GdiplusShutdown(gdiplusToken);
+
+    return result;
+}
diff --git a/native/libwinbridge/bridge.h b/native/libwinbridge/bridge.h
index 85d86ad..77fa4d4 100644
--- a/native/libwinbridge/bridge.h
+++ b/native/libwinbridge/bridge.h
@@ -146,4 +146,9 @@ extern "C" int32_t get_clipboard(wchar_t * buffer, int32_t size);
  */
 extern "C" int32_t set_clipboard(wchar_t * text);
 
+/*
+ * Set the clipboard image to the given path
+ */
+extern "C" int32_t set_clipboard_image(wchar_t * path);
+
 #endif //ESPANSO_BRIDGE_H
\ No newline at end of file
diff --git a/src/bridge/windows.rs b/src/bridge/windows.rs
index db9833e..ff916fa 100644
--- a/src/bridge/windows.rs
+++ b/src/bridge/windows.rs
@@ -47,6 +47,7 @@ extern {
     // CLIPBOARD
     pub fn get_clipboard(buffer: *mut u16, size: i32) -> i32;
     pub fn set_clipboard(payload: *const u16) -> i32;
+    pub fn set_clipboard_image(path: *const u16) -> i32;
 
     // KEYBOARD
     pub fn register_keypress_callback(cb: extern fn(_self: *mut c_void, *const u16,
diff --git a/src/clipboard/windows.rs b/src/clipboard/windows.rs
index caa8e0e..63fa070 100644
--- a/src/clipboard/windows.rs
+++ b/src/clipboard/windows.rs
@@ -18,7 +18,8 @@
  */
 
 use widestring::U16CString;
-use crate::bridge::windows::{set_clipboard, get_clipboard};
+use crate::bridge::windows::{set_clipboard, get_clipboard, set_clipboard_image};
+use std::path::Path;
 
 pub struct WindowsClipboardManager {
 
@@ -53,4 +54,12 @@ impl super::ClipboardManager for WindowsClipboardManager {
             set_clipboard(payload_c.as_ptr());
         }
     }
+
+    fn set_clipboard_image(&self, image_path: &Path) {
+        let path_string = image_path.to_string_lossy().into_owned();
+        unsafe {
+            let payload_c = U16CString::from_str(path_string).unwrap();
+            set_clipboard_image(payload_c.as_ptr());
+        }
+    }
 }
\ No newline at end of file
diff --git a/src/engine.rs b/src/engine.rs
index d0163e6..19f96f8 100644
--- a/src/engine.rs
+++ b/src/engine.rs
@@ -218,14 +218,12 @@ impl <'a, S: KeyboardManager, C: ClipboardManager, M: ConfigManager<'a>, U: UIMa
 
             // Image Match
             MatchContentType::Image(content) => {
-                let image_path = PathBuf::from(&content.path);
-
                 // Make sure the image exist beforehand
-                if image_path.exists() {
-                    self.clipboard_manager.set_clipboard_image(&image_path);
+                if content.path.exists() {
+                    self.clipboard_manager.set_clipboard_image(&content.path);
                     self.keyboard_manager.trigger_paste();
                 }else{
-                    error!("Image not found in path: {:?}", image_path);
+                    error!("Image not found in path: {:?}", content.path);
                 }
             },
         }
diff --git a/src/matcher/mod.rs b/src/matcher/mod.rs
index 2811a07..947dce0 100644
--- a/src/matcher/mod.rs
+++ b/src/matcher/mod.rs
@@ -22,6 +22,8 @@ use crate::event::{KeyEvent, KeyModifier};
 use crate::event::KeyEventReceiver;
 use serde_yaml::Mapping;
 use regex::Regex;
+use std::path::PathBuf;
+use std::fs;
 
 pub(crate) mod scrolling;
 
@@ -53,7 +55,7 @@ pub struct TextContent {
 
 #[derive(Debug, Serialize, Clone)]
 pub struct ImageContent {
-    pub path: String,
+    pub path: PathBuf,
 }
 
 impl <'de> serde::Deserialize<'de> for Match {
@@ -97,8 +99,29 @@ impl<'a> From<&'a AutoMatch> for Match{
 
             MatchContentType::Text(content)
         }else if let Some(image_path) = &other.image_path {  // Image match
+            // On Windows, we have to replace the forward / with the backslash \ in the path
+            let new_path = if cfg!(target_os = "windows") {
+                image_path.replace("/", "\\")
+            }else{
+                image_path.to_owned()
+            };
+
+            // Calculate variables in path
+            let new_path = if new_path.contains("$CONFIG") {
+                let config_dir = crate::context::get_config_dir();
+                let config_path = fs::canonicalize(&config_dir);
+                let config_path = if let Ok(config_path) = config_path {
+                    config_path.to_string_lossy().into_owned()
+                }else{
+                    "".to_owned()
+                };
+                new_path.replace("$CONFIG", &config_path)
+            }else{
+                new_path.to_owned()
+            };
+
             let content = ImageContent {
-                path: image_path.clone()
+                path: PathBuf::from(new_path)
             };
 
             MatchContentType::Image(content)